Jackson was nicknamed "Mr. October" for his clutch hitting in the postseason with the Athletics and the Yankees.[1] Jackson helped Oakland win five consecutive American League West divisional pennants, three consecutive American League pennants and two consecutive World Series titles (he did not play in the 1972 World Series due to injury), from 1971 to 1975. He helped New York win four American League East divisional pennants, three American League pennants and two consecutive World Series titles, from 1977 to 1981. He also helped the California Angels win two American League West divisional pennants in 1982 and 1986. He is perhaps best remembered for hitting three consecutive home runs in the clinching game of the 1977 World Series.[1]

Jackson was born in the Wyncote neighborhood of Cheltenham Township, just north of Philadelphia. His father was Martinez Jackson, a half Puerto Rican man[4] who worked as a tailor and who also was a former second baseman with the Newark Eagles of the Negro Leagues.[5] He was the youngest of four children from his mother, Clara, who was of Puerto Rican descent. He also had two half-siblings from his father's first marriage.[6] His parents divorced when he was four; his mother taking four of his siblings with her, while his father took Jackson, and one of the siblings from his first marriage, though one sibling later returned to Wyncote.[6] His father (as a single parent) raised his son, and theirs was one of the few black families in Wyncote. He was able to develop a social ease with the Jewish community in Wyncote, as all his friends, girlfriends, coaches, and teachers during that timeframe were Jewish.[7] In 1972 Jackson joined his Jewish teammates on the A's - Ken Holtzman and Mike Epstein - in wearing black armbands for the rest of the postseason after the Munich Massacre. At Cheltenham High School he was a classmate of Yonatan Netanyahu, who 12 years after graduation led the Israeli raid on Entebbe, in 1976.

Jackson graduated from Cheltenham High in 1964, where he excelled in football, basketball, baseball, and track and field.[8] In his junior year of high-school, Jackson, a tailback, tore up his knee in an early season game. He was told by the doctors he was never to play football again, but Jackson returned for the final game of the season.[9] In that game Jackson fractured five cervical vertebrae, which caused him to spend six weeks in the hospital and another month in a neck cast. Doctors told Jackson that he might never walk again, let alone play football, but Jackson defied the odds again.[9] On the baseball team, he batted .550 and threw several no-hitters.[10] In the middle of his senior year, Jackson's father was arrested for bootlegging and was sentenced to six months in jail.[10]

In football, he was scouted by Alabama, Georgia, and Oklahoma, all of whom were willing to break the color barrier just for Jackson (Oklahoma had Black football players before 1964- including Prentice Gautt, a star running back recruited in 1957, who played in the NFL with the St. Louis Cardinals).[10] Jackson declined Alabama and Georgia because he was fearful of the South at the time, and declined Oklahoma because they told him to stop dating white girls.[10] For baseball, Jackson was scouted by Hans Lobert of the San Francisco Giants who was desperate to sign him.[10] The Los Angeles Dodgers and Minnesota Twins also made offers, and the hometown Philadelphia Phillies gave him a tryout but declined because of his "hitting skills".[11] His father wanted his son to go to college,[11] where Jackson wanted to play both football and baseball.[11] He decided to attend Arizona State University on a football scholarship. His high-school football coach knew the football coach for Arizona State Frank Kush, and they discussed the possibility of him playing both sports. After a recruiting trip, Kush decided that Jackson had the ability and willingness to work to join the squad.[11]

One day after football practice, he approached baseball coach Bobby Winkles asking if he could join the team. Winkles said he would give Jackson a look, and the next day while still in his football gear, he hit a home run on the second pitch he saw. In five at bats he hit three home runs.[12] He was allowed to practice with the team, but could not join the squad because the NCAA had a rule forbidding the use of freshman players.[12] Jackson switched permanently to baseball following his freshman year, as he did not want to become a defensive back.[13] To hone his skills, Winkles assigned him to a Baltimore Orioles-affiliated amateur team. He broke numerous team records for the squad, and the Orioles offered him a $50,000 signing bonus if he joined the team.[14] Jackson declined the offer stating that he did not want to forfeit his college scholarship.[12] In the beginning of his sophomore year Jackson replaced Rick Monday (who was the first player ever drafted in the Major League Baseball Draft) at center field. During that season he broke the team record for most home runs in a single season, led the team in numerous other categories and was first team All-American.[15] Many scouts were looking at him play, including Tom Greenwade of the New York Yankees (who discovered Mickey Mantle), and Danny Murtaugh of the Pittsburgh Pirates.[15] In his final game at Arizona State, he showed his potential by being only a triple away from hitting for the cycle, making a sliding catch, and having an assist at home plate.[15] Jackson was the first college player to hit a home run out of Phoenix Municipal Stadium.[16]

Jackson progressed through the minors quickly, reporting for his first training camp with the Single-A Lewis-Clark Broncs, Lewiston, Idaho in June 1966, having signed for $85,000 (source: "40 Years Ago Today" in the Lewiston Morning Tribune June 15, 2006,[20]) and playing one season for the A's Single-A teams, the Broncs and Modesto, California and one more season for their Double-A affiliate in Birmingham, Alabama. It was in Birmingham that Jackson got his first taste of racism, being one of only a few blacks on the team.[21] He credits the team's manager at the time, John McNamara, who had previously been the Broncs' catcher-manager, for helping him through that difficult season.

Jackson signing autographs for some fans in Tiger Stadium during the 1974 season.

Jackson debuted in the major leagues with the A's on June 9, 1967, a pair of A's victories by scores of 2-0 and 6–0 over the Cleveland Indians in Cleveland. (Jackson had his first career hit, a triple versus reliever Orlando Pena, in the nightcap.) Following that season, the Athletics moved to Oakland. Jackson hit 47 home runs in 1969, and was briefly ahead of the pace that Roger Maris set when he broke the single-season record for home runs with 61 in 1961, and that of Babe Ruth when he set the previous record of 60 in 1927. Jackson later said that the sportswriters were claiming he was "dating a lady named 'Ruth Maris.'" That off-season, Jackson sought an increase in salary, and Athletics owner Charlie O. Finley threatened to send Jackson to the minors. Commissioner Bowie Kuhn successfully intervened in their dispute, but Jackson's numbers in 1970 dropped sharply, as he hit just 23 home runs while batting .237. The Athletics sent him to play in Puerto Rico. There he played for the Santurce team and hit 20 homers and knocked in 47 runs to lead the league in both departments. Jackson hit a memorable home run in the 1971 All-Star Game at Tiger Stadium in Detroit. Batting for the American League against Pittsburgh Pirates pitcher Dock Ellis, the ball he hit soared above the right-field stands, striking the transformer of a light standard on the right field roof. In 1984, he would hit a home run over that roof.

In 1971, the Athletics won the American League's Western Division title, their first first-place finish since 1931, when they played in Philadelphia. They lost the American League Championship Series to the Baltimore Orioles. The A's won the Division again in 1972; their series with the Tigers went five games, and Jackson scored the tying run in the clincher on a steal of home. In the process, however, he tore a hamstring and was unable to play in the World Series. The A's still managed to defeat the Cincinnati Reds in seven games. It was the first championship won by a San Francisco Bay Area team in any major league sport.

During spring training in 1972, Jackson showed up with a mustache. Though his teammates wanted him to shave it off, Jackson refused. Finley liked the mustache so much that he offered each player $300 to grow one, and hosted a "Mustache Day" featuring the last MLB player to wear a mustache, Frenchy Bordagaray, as master of ceremonies.[22]

Jackson helped the Athletics win the pennant again in 1973, and was named Most Valuable Player of the American League for the season. The A's defeated the New York Mets in seven hard-fought games in the World Series. This time, Jackson was not only able to play, but his performance led to his being awarded the Series' Most Valuable Player award. In the third inning of that seventh game, which ended in a 5–2 score, the A's jumped out to a 4–0 lead as both Bert Campaneris and Jackson hit two-run home runs off Jon Matlack—the only two home runs Oakland hit the entire Series. The A's won the World Series again in 1974, defeating the Los Angeles Dodgers in five games.

Besides putting up monster numbers during his nine years with the Athletics, including 254 home runs, Jackson was also no stranger to controversy or conflict in Oakland. Sports author Dick Crouser wrote, "When the late Al Helfer was broadcasting the Oakland A's games, he was not too enthusiastic about Reggie Jackson's speed or his hustle. Once, with Jackson on third, teammate Rick Monday hit a long home run. 'Jackson should score easily on that one,' commented Helfer. Crouser also noted that, "Nobody seems to be neutral on Reggie Jackson. You're either a fan or a detractor." One-time teammate Darold Knowles would seem to be in the latter camp. Once when asked if Jackson was a hotdog (i.e., a show-off), he famously replied, "There isn't enough mustard in the world to cover Reggie Jackson."[23]

Perhaps the most notable off-field incident involving Jackson occurred on June 5, 1974, when outfielder Billy North and Jackson engaged in a clubhouse fight at Detroit's Tiger Stadium. Jackson injured his shoulder, and catcher Ray Fosse, attempting to separate the combatants, suffered a crushed disk in his neck, costing him three months on the disabled list.

The A's won the division again in 1975, but the loss of pitcher Catfish Hunter, baseball's first modern free agent, left them vulnerable, and they were swept in the ALCS by the Boston Red Sox. With the coming of free agency after the 1976 season, and with team owner Finley unwilling to pay the higher salary that Jackson would ask for, Jackson was traded on April 2, 1976 along with minor leaguer Bill VanBommell and Ken Holtzman to the Baltimore Orioles for Don Baylor, Mike Torrez, and Paul Mitchell. Both his new team, the Orioles, and his former team, the Athletics, finished second in their respective divisions.

The Yankees signed Jackson to a five-year contract totaling $2.96 million ($12,267,556 in current dollar terms) on November 29, 1976.[24][25] Upon arriving in New York, the number 9 that he had worn in Oakland and Baltimore was worn by third baseman Graig Nettles. Jackson asked for number 42, in memory of Jackie Robinson, but manager Billy Martin brought his friend Art Fowler in as pitching coach, and gave him number 42. So, noting that then-all-time home run leader Hank Aaron had just retired, Jackson asked for and received number 44, Aaron's number. On his first day in spring training the following February, however, Jackson wore number 20 (the number of Frank Robinson, who had also just retired) before switching to 44.

Jackson's first season with the Yankees, 1977, was a difficult one. Although team owner George Steinbrenner and several players, most notably catcher and team captain Thurman Munson and outfielder Lou Piniella, were excited about his arrival, Martin was not. Martin had managed the Tigers in 1972, when Jackson's A's beat them in the playoffs. Jackson was once quoted as saying of Martin, "I hate him, but if I played for him, I'd probably love him."

The relationship between Jackson and his new teammates was strained due to an interview with SPORT magazine writer Robert Ward. During spring training at the Yankees' camp in Fort Lauderdale, Florida, Jackson and Ward were having drinks at a nearby bar. Jackson's version of the story is that he noted that the Yankees had won the pennant the year before, but lost the World Series to the Reds, and suggested that they needed one thing more to win it all, and pointed out the various ingredients in his drink. Ward suggested that Jackson might be "the straw that stirs the drink." But when the story appeared in the May 1977 issue of SPORT, Ward quoted Jackson as saying, "This team, it all flows from me. I'm the straw that stirs the drink. Maybe I should say me and Munson, but he can only stir it bad."

Jackson signs with the Yankees.

Jackson has consistently denied saying anything negative about Munson in the interview and that his quotes were taken out of context.[26] However, Dave Anderson of the New York Times subsequently wrote that he had drinks with Jackson in July 1977, and that Jackson told him, "I'm still the straw that stirs the drink. Not Munson, not nobody else on this club."[27] Regardless, as Munson was beloved by his teammates, Martin, Steinbrenner and Yankee fans, the relationships between them and Jackson became very strained.

On June 18, in a 10–4 loss to the Boston Red Sox in a nationally televised game at Fenway Park in Boston, Jim Rice, a powerful hitter but notoriously slow runner, hit a ball into shallow right field that Jackson appeared to weakly attempt to field. Jackson failed to reach the ball which fell far in front of him, thereby allowing Rice to reach second base. Furious, Martin removed Jackson from the game without even waiting for the end of the inning, sending Paul Blair out to replace him. When Jackson arrived at the dugout, Martin yelled that Jackson had shown him up. They argued, and Jackson said that Martin's heavy drinking had impaired his judgment. Despite Jackson being 18 years younger, about two inches taller and maybe 40 pounds heavier, Martin lunged at him, and had to be restrained by coaches Yogi Berra and Elston Howard. Red Sox fans could see this in the dugout and began cheering wildly, and the NBC TV cameras showed the confrontation to the entire country.

Yankees management defused the situation by the next day, but the relationship between Jackson and Martin was permanently poisoned. However, George Steinbrenner made a crucial intervention when he gave Martin the option of either having Jackson bat in the fourth or "cleanup" spot for the rest of the season, or losing his job. Martin made the change and Jackson's hitting improved (he had 13 home runs and 49 RBIs over his next 50 games), and the team went on a winning streak. On September 14, while in a tight three-way race for the American League Eastern Division crown with the Red Sox and Orioles, Jackson ended a game with the Red Sox by hitting a home run off Reggie Cleveland, giving the Yankees a 2–0 win. The Yankees won the division by two and a half games over the Red Sox and Orioles, and came from behind in the top of the ninth inning in the fifth and final game of the American League Championship Series to beat the Kansas City Royals for the pennant.

During the 1977 World Series against the Dodgers, Munson was interviewed, and suggested that Jackson, because of his past post-season performances, might be the better interview subject. "Go ask Mister October," he said, giving Jackson a nickname that would stick. (In Oakland, he had been known as "Jax" and "Buck.") Jackson hit home runs in Games Four and Five of the Series.

Jackson's crowning achievement came with his three-home-run performance in World Series-clinching Game Six, each on the first pitch, off three Dodgers pitchers. (His first plate-appearance, during the second inning, resulted in a four-pitch walk.) The first came off starter Burt Hooton, and was a line drive shot into the lower right field seats at Yankee Stadium. The second was a much faster line drive off reliever Elías Sosa into roughly the same area. With the fans chanting his name, "Reg-GIE! Reg-GIE! Reg-GIE!" the third came off reliever Charlie Hough, a knuckleball pitcher, making the distance of this home run particularly remarkable. It was a towering drive into the black-painted batter's eye seats in center, 475 feet away.

Since Jackson had hit a home run off Dodger pitcher Don Sutton in his last at bat in Game Five, his three home runs in Game Six meant that he had hit four home runs on four consecutive swings of the bat against as many Dodgers pitchers. Jackson became the first player to win the World Series MVP award for two teams. In 27 World Series games, he amassed 10 home runs, including a record five during the 1977 Series (the last three on first pitches), 24 RBI and a .357 batting average. Babe Ruth, Albert Pujols, and Pablo Sandoval are the only other players to hit three home runs in a single World Series game. Babe Ruth accomplishing the feat twice - in 1926 and 1928 (both in Game Four). With 25 total bases, Jackson also broke Ruth's record of 22 in the latter Series; this remains a World Series record, Willie Stargell tying it in the 1979 World Series. In 2009, Chase Utley of the Philadelphia Phillies tied Jackson's record for most home runs in a single World Series.

An often forgotten aspect of the ending of this decisive Game 6 was the way Jackson left the field at the game's end. Ironically, despite everything Jackson had done for the Yankees that night, the uncontrollable behavior of Yankee Stadium fans left him feeling understandably worried for his safety. Fans had been getting somewhat rowdy in anticipation of the game's end, and some had actually thrown firecrackers out near Jackson's area in right field. Jackson was alarmed enough about this to walk off the field, in order to get a helmet from the Yankee bench to protect himself. Shortly after this point, as the end of the game neared, fans were actually bold enough to climb over the wall, draping their legs over the side in preparation for the moment when they planned to rush onto the field. When that moment came, after pitcher Mike Torrez caught a pop-up for the game's final out, Jackson started running at top speed off the field, actually body-checking past some of these fans filling the playing field in the manner of a football linebacker.[28]

The Yankees' home opener of the 1978 season, on April 13 against the Chicago White Sox, featured a new product, the "Reggie!" bar. In 1976, while playing in Baltimore, Jackson had said, "If I played in New York, they'd name a candy bar after me." The Standard Brands company responded with a circular "bar" of peanuts dipped in caramel and covered in chocolate, a confection which was originally named the "Wayne Bun" as it was made in Fort Wayne, Indiana. The "Reggie!" bars were handed to fans as they walked into Yankee Stadium. Jackson hit a home run, and when he returned to right field the next inning, fans began throwing the Reggie bars on the field in celebration. Jackson told the press that this confused him, thinking that maybe the fans did not like the candy.[29] The Yankees won the game, 4–2.

But the Yankees could not maintain their success, as manager Billy Martin lost control. On July 23, after suspending Jackson for disobeying a sign during a July 17 game, Martin made a statement about his two main antagonists, referring to comments Jackson had made and team owner George Steinbrenner's 1972 violation of campaign-finance laws: "They're made for each other. One's a born liar, the other's convicted." It was moments like these that gave the Yankees the nickname "The Bronx Zoo."

Martin resigned the next day (some sources have said he was actually fired[30]), and was replaced by Bob Lemon, a Hall of Fame pitcher for the Cleveland Indians who had been recently fired as manager of the White Sox. Steinbrenner, a Cleveland-area native, had hired former Indians star Al Rosen as his team president (replacing another Cleveland figure, Gabe Paul). Steinbrenner jumped at the chance to involve another hero of his youth with the Yankees; Lemon had been one of Steinbrenner's coaches during the Bombers' pennant-winning 1976 season.

After being 14 games behind the first-place Red Sox on July 18, the Yankees finished the season in a tie for first place. The two teams played a one-game playoff for the division title at Fenway Park, with the Yankees winning 5–4. Although the home run by light-hitting shortstop Bucky Dent in the seventh inning got the most notice, it was an eighth-inning home run by Jackson that gave the Yankees the fifth run they ended up needing. The next day, with the American League Championship Series with the Royals beginning, Jackson hit a home run off the Royals' top reliever at the time, Al Hrabosky, the flamboyant "Mad Hungarian." The Yankees won the pennant in four games, their third straight.

Jackson was once again in the center of events in the World Series, again against the Dodgers. Los Angeles won the first two games at Dodger Stadium, taking the second when rookie reliever Bob Welch struck Jackson out with two men on base with two outs in the ninth inning. The series then moved to New York, and after the Yankees won Game Three on several fine defensive plays by third baseman Graig Nettles, Game Four saw Jackson in the middle of a controversial play on the basepaths. In the sixth inning, after collecting an RBI single, Jackson was struck in the hip–possibly on purpose–by a ball thrown by Dodger shortstop Bill Russell as Jackson was being forced at second base. Instead of completing a double play that would have ended the inning, the ball caromed into foul territory and allowed Thurman Munson to score the Yankees' second run of the inning. In spite of the Dodgers' protests of interference on Jackson's part, the umpires allowed the play to stand. The Yankees tied the game in the eighth inning and eventually won in the tenth.

Following a blowout win in Game Five, both teams headed back to Los Angeles. In Game Six, Jackson got his revenge against Welch by blasting a two-run home run in the seventh inning, putting the finishing touch on a series-clinching, 7-2 win for the Yankees.

As he entered the last year of his Yankee contract in 1981, Jackson endured several difficulties from George Steinbrenner. After the owner consulted Jackson about signing then-free agent Dave Winfield, Jackson expected Steinbrenner to work out a new contract for him as well. Steinbrenner never did (some say never intending to) and Jackson played the season as a free agent. Jackson started slowly with the bat, and when the 1981 Major League Baseball strike began, Steinbrenner invoked a clause in Jackson's contract forcing him to take a complete physical examination. Jackson was outraged and blasted Steinbrenner in the media. When the season resumed, Jackson's hitting improved, partly to show Steinbrenner he wasn't finished as a player. He hit a long home run into the upper deck in Game Five of the strike-forced 1981 American League Division Series with the Brewers, and the Yankees went on to win the pennant again. However, Jackson injured himself running the bases in Game Two of the 1981 ALCS and missed the first two games of the World Series, both of which the Yankees won.

Jackson was medically cleared to play Game Three, but manager Bob Lemon refused to start him or even play him, allegedly acting under orders from Steinbrenner. The Yankees lost that game and Jackson played the remainder of the series, hitting a home run in Game Four. However, they lost the last three games and the World Series to the Dodgers.

Jackson became a free-agent again once the 1981 season was over. The owner of the California Angels, entertainer Gene Autry, had heard of Jackson's desire to return to California to play, and signed him to a five-year contract.

On April 27, 1982, in Jackson's first game back at Yankee Stadium with the Angels, he broke out of a terrible season-starting slump to hit a home run off former teammate Ron Guidry. The at-bat began with Yankee fans, angry at Steinbrenner for letting Jackson get away, starting the "Reg-GIE!" chant, and ended it with the fans chanting "Steinbrenner sucks!" By the time of Jackson's election to the Hall of Fame, Steinbrenner had begun to say that letting him go was the biggest mistake he has made as Yankee owner.

That season, the Angels won the American League West, and would do so again in 1986, but lost the American League Championship Series both times. On September 17, 1984, on the 17th anniversary of the day he hit his first home run, he hit his 500th, at Anaheim Stadium off Bud Black of the Royals.

In 1987, he signed a one-year contract to return to the A's, wearing the number 44 with which he was now most associated rather than the number 9 he previously wore in Oakland. He announced he would retire after the season, at the age of 41. In his last at-bat, at Comiskey Park in Chicago on October 4, he collected a broken-bat single up the middle, but the A's lost to the White Sox, 5–2. He is the last Kansas City A's player to play in a Major League Baseball game.

Jackson played 21 seasons and reached the post-season in 11 of them, winning six pennants and five World Series. His accomplishments include winning both the regular-season and World Series MVP awards in 1973, hitting 563 career home runs (sixth all-time at the time of his retirement), maintaining a .490 career slugging percentage, being named to 14 All-Star teams, and the dubious distinction of being the all-time leader in strikeouts with 2,597 (he finished with 13 more career strikeouts than hits) and second on the all time list for most Golden sombreros (at least four strikeouts in a game) with 23 - he led this statistic until 2014, when he was surpassed by Ryan Howard. Jackson was the first major leaguer to hit one hundred home runs for three different clubs, having hit over 100 for the Athletics, Yankees, and Angels. Reggie Jackson is the only player in the 500 home run club that never had consecutive 30 home run seasons in a career.

During his freshman year at Arizona State, he met Jennie Campos, a Mexican-American.[13] Jackson asked Campos on a date, and discovered many similarities, including the ability to speak Spanish, and being raised in a single parent home (Campos's father was killed in the Korean War).[13] An assistant football coach tried to break up the couple because Jackson was black and Campos was considered white. The coach contacted Campos's uncle, a wealthy benefactor of the school, and he warned the couple that their being together was a bad idea.[31] But the relationship held up and she later became his first wife. Jackson has been divorced since 1973. Kimberly, his only child, was born in the late 1980s.[32]

He co-authored a book in 2010, Sixty-Feet Six-Inches, with fellow Hall of Famer Bob Gibson. The book, whose title refers to the distance between the pitcher's mound and home plate, details their careers and approach to the game.

The SegaMaster System baseball video game Reggie Jackson Baseball, endorsed by Reggie Jackson, was sold exclusively in the United States. Outside of the U.S., it was released as American Baseball.

Jackson has endured three fires to personal property, including a 1991 fire to his home in Oakland which destroyed his 1973 MVP Award. One of his warehouses holding several of his collectible cars was damaged in a fire, with several of the cars, valued at $3.2 million, ruined.[32]

Jackson and Steinbrenner would reconcile, and Steinbrenner would hire him as a "special assistant to the principal owner", making Jackson a consultant and a liaison to the team's players, particularly the minority players. By this point, the Yankees, long noted for being slow to adapt to changes in race relations, have come to develop many minority players in their farm system and seek out others via trades and free agency. Jackson usually appears in uniform at the Yankees' current spring training complex in Tampa, Florida, and has been sought out for advice by current stars such as Derek Jeter and Alex Rodriguez. "His experience is vast, and he's especially good with the young players in our minor league system, the 17- and 18-year old kids. They respect him and what he's accomplished in his career. When Reggie Jackson tells a young kid how he might improve his swing, he tends to listen", said Hal Steinbrenner, Yankees' managing general partner and co-chairperson.[32]

Jackson was inducted to the Hall of Fame in 1993.[34] He chose to wear a Yankees cap on his Hall of Fame plaque[35] after the Oakland Athletics unceremoniously fired him from a coaching position in 1991.[36]

The Yankees retired his uniform number 44 on August 14, 1993, shortly after his induction into the Hall of Fame. The Athletics retired his number 9 on May 22, 2004. He is one of only eight MLB players to have their numbers retired by more than one team, and one of only three to have different numbers retired by two MLB teams.

In 1999, Jackson placed 48th on Sporting News 100 Greatest Baseball Players. That same year, he was named one of 100 finalists for the Major League Baseball All-Century Team, but was not one of the 30 players chosen by the fans.

The Yankees dedicated a plaque in his honor on July 6, 2002, which now hangs in Monument Park at Yankee Stadium. The plaque calls him "One of the most colorful and exciting players of his era" and "a prolific hitter who thrived in pressure situations." Each Yankee so honored and still living was on hand for the dedication: Phil Rizzuto, Yogi Berra, Whitey Ford and Don Mattingly. Ron Guidry, a teammate of Jackson's for all five of his seasons with the Yankees, was there, and would be honored with a Monument Park plaque the next season. Out of respect to some of the players who Jackson admired while growing up, Jackson invited Willie Mays, Hank Aaron and Ernie Banks to attend the ceremony, and each did so. Like Jackson, each was a member of the Hall of Fame and had hit over 500 career home runs. Each had also played in the Negro Leagues.

Jackson expanded his love of antique cars into a chain of auto dealerships in California, and used his contacts to become one of the foremost traders of sports memorabilia.[37] He has also been the public face of a group attempting to purchase a major league team, already having made unsuccessful attempts to buy the Athletics and the Angels.[38] His attempt to acquire the Angels along with Jimmy Nederlander (minority owner of the New York Yankees), Jackie Autry (widow of former Angels owner Gene Autry) and other luminaries was thwarted by Mexican American billionaire Arturo Moreno who outbid Jackson's group by nearly $50 million for the team in the winter of 2002.[39]

In a July edition of Sports Illustrated, Jackson talked about several issues, and also was critical of the Baseball Writers' Association of America as he believes they have lowered their standards when voting for prospects in the Hall of Fame.[32] He has also been critical of players associated with performance-enhancing drugs (PEDs), including distant cousin Barry Bonds, stating "I believe that Hank Aaron is the home run king, not Barry Bonds, as great of a player Bonds was."[32] Of Alex Rodriguez, whom Jackson has worked alongside as special assistant to the Yankees, Jackson remarked, "Al's a very good friend. But I think there are real questions about his numbers. As much as I like him, what he admitted about his usage does cloud some of his numbers."[32] On July 12, the Yankees released a statement from Jackson after the Sports Illustrated interview had been released. The press release included Jackson saying, "In trying to convey my feelings about a few issues that I am passionate about, I made the mistake of naming some specific players."[40] It had been reported [41] he had been told by the Yankees to steer clear from the team, although general manager Brian Cashman stated he had not been banned but only told to not join the club on a road trip to Boston and would later be free to interact with the club.[42] After the SI article became known and Jackson's status with the Yankees being talked about, Jackson confirmed in his statement "I continue to have a strong relationship with the club, and look forward to continuing my role with the team."[40]

In 2007, ESPN aired a mini-series called The Bronx is Burning, about the 1977 Yankees, with the conflicts and controversies around Jackson a central part of the storyline. Jackson is portrayed by Daniel Sunjata. In 2008, he threw out the first pitch at Yankees Opening Day, the last one at Yankee Stadium. He also threw out the first pitch at the first game at the new Yankee Stadium (an exhibition game).